Tributylstannane → methyl 2-[(4R)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

HRID 851371ノート

反応式

HRID 851371 の反応式
[CH2:1]([C@H:4]1[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:16])[CH:5]1Cl)[CH:2]=[CH2:3].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C@H:4]1[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:16])[CH2:5]1)[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 516892Sodium BicarbonateHCID 54283209methyl 2-[(4R)-4-allyl-3-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

生成物 1

HCID 54326273methyl 2-[(4R)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate収率 87%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl 2-[(4R)-4-allyl-3-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (600 mg), tributyltinhydride (0.97 ml) and 2,2'-azobis-(2-methylpropionitrile) (40 mg) in benzene (6 ml) was refluxed for 1.5 hours. The reaction mixture was poured into a mixture of ethyl acetate (30 ml) and dilute aqueous sodium bicarbonate. The organic layer was separated, and washed with brine, dried over magnesium sulfate and evaporated in vacuo. The oily residue was chromatographed on silica gel (10 g) eluting with a mixture of hexane and ethyl acetate (10:1-10:3) to give methyl 2-[(4R)-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (452 mg) as an oil.

後処理

  1. temperaturewas refluxed for 1.5 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe oily residue was chromatographed on silica gel (10 g)
  7. washeluting with a mixture of hexane and ethyl acetate (10:1-10:3)

出典と根拠

ORDレコード
ord-77574fc5bb5d4e5c982b7335b2da0aca
出典データセット
uspto-grants-1983_05
特許番号
US04383945

反応ノート

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